Vacation rentals in Canaan

Cabin Nestled in the Litchfield Hills

Cozy, curated cabin in NW Connecticut—just over 2 hrs from NYC by car or train. Nestled above the Housatonic River, it’s a place to hike, antique, or do nothing at all. Watch wild turkeys, deer, rabbits, and the occasional fox wander through the yard. Toast s’mores by the fire pit, then stargaze beneath a wide, quiet sky. The Appalachian Trail and some of the best hikes in the Northeast are just steps away. A peaceful escape in every season—recharge with nature, friends, or the stillness itself.

Secret Hideaway @hightonic_life

The real meaning of escape. As you drive up the dirt road driveway, feel your worries disappear as you arise to the top of the Mountain. The views of the Catskills are breathtaking. At this elevation we have a unique weather pattern - at times, above the clouds. Hike the 100 acre property and sip some coffee or tea atop a selection of tree stands scattered throughout the land. We have a natural pool most of the time and the hand built fireplace is so warm you might even take a dip in winter.

The Red Cabin-Secluded Getaway with backyard Brook

Welcome to our secluded mid-century cabin nestled in the foothills of the Berkshires in Northwestern CT! When you stay here you'll find over three private acres of ferns, forests, wild flowers and a native trout brook a stone's throw from the backdoor with your private hot tub to relax in. Beyond the brook are hundreds of acres of state forest preserve. Enjoy great hiking, fishing, skiing, antiques and restaurants minutes away. Only 2 hours from NYC and 8 minutes to Historic Norfolk Center.

Hideaway with Spectacular Berkshire Views

Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.

Newly Built Cottage in Housatonic Valley

This newly built modern cottage is located on a historic railroad street nestled in a charming village within the Housatonic River Valley. There are beautiful river views from the front porch, deep woods off the back deck, a white marble kitchen with new appliances, and a dedicated parking spot. Escape the city and surround yourself in this quiet valley and the calm of small village life, located just 2 hours from NYC. This location offers year-round access to nature & outdoor activities.

Walk to Brewery in Historic Railroad Depot

This light-filled space is in a separate wing of my house with its own private entrance. There is one bedroom with a king-sized bed, spacious living room with table for meals, a large TV, a refrigerator/freezer stocked with bottled water and 1/2&1/2 for coffee, microwave and coffee maker with coffee pods are provided. You will hear the train as it travels through town. There are several places to eat nearby. Be sure to check out GUIDEBOOK on my listing to see what our area offers!!!

Cozy Railroad Street Retreat

Enjoy a peaceful stay at the Railroad Street Retreat, originally built in the 1840s, and recently renovated. This cozy 540-square-foot guest suite is perfect for a romantic getaway, a writing retreat, a leaf-peeping tour, and more. Located in the heart of the village, you are a few minutes' walk from Off the Trail Cafe, the Appalachian Trail, the Falls Village Inn taproom and restaurant, and a short drive from antique shops, breweries, markets, galleries, cafes, and more.

Unique, Rustic, and Beautiful

Utterly unique, handcrafted wooden home, 4 bedrooms to sleep 6-7 (2 kings, 2 twins, daybed/couches in living room/den. 15 minutes from Mohawk Mountain Ski Area, Lakeville, Cornwall, and North Canaan. Two fireplaces. Nine acres of property surrounded by forest above the Hollenbeck River, with surrounding farmland and mountains. Patio, grill, firepit, and a hill for sledding. Perfect for a winter getaway with friends or family, summer barbeques, or daily hiking or fishing.

Private rooms and full bath in a Historic Home

Our home is in a quaint New England town in Northwest Connecticut. We are a fan of historic houses and our house dates back to 1734. You have your own private entrance, two spacious rooms, and a full bath. The bedroom upstairs also has a small fridge, coffee maker, and electric tea kettle. The full bathroom is downstairs on the main floor. You will be close to town, so you have a restaurant, cafe, design store, library, and post office all in walking distance.